Imidazole → tert-butyl[(1R,2R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-1-phenylpropyl]carbamate

HRID 64443Notes

Reaction equation

HRID 64443 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:9]([OH:12])[CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21].N1C=CN=C1.ClCCl>C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C@@H:9]([OH:12])[CH2:10][O:11][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 10890842tert-butyl[(1R,2R)-2,3-dihydroxy-1-phenylpropyl]carbamate

Product 1

HCID 10738641tert-butyl[(1R,2R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-1-phenylpropyl]carbamateYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 620 mg of tert-butyl[(1R,2R)-2,3-dihydroxy-1-phenylpropyl]carbamate, 0.37 g of tert-butyldimethylchlorosilane, 0.19 g of imidazole, and 9.3 ml of dichloromethane was stirred for 2 hours. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 705 mg of tert-butyl[(1R,2R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxy-1-phenylpropyl]carbamate.

Workup

  1. customa layer separation operation
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9ccf01dccc8463da26e84bb8541a7a3
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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